Water → 2-Iodo-4-(propan-2-yl)phenol

HRID 437206Notes

Reaction equation

HRID 437206 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:3].[I:11]Cl.O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[I:11][C:6]1[CH:5]=[C:4]([CH:2]([CH3:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 74654-IsopropylphenolHCID 24640Iodine chlorideHCID 23665763Sodium Bisulfite

Product 1

HCID 126521002-Iodo-4-(propan-2-yl)phenolYield 49.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-(1-Methylethyl)phenol (27.2 g., 0.20 moles) is dissolved in acetic acid (100 ml.). Iodine monochloride (32.5 g., 0.20 mole) in acetic acid (50 ml.) is then added slowly. The dark mixture is refluxed for 6 hours, cooled and poured into cold water (1 l.) containing a little sodium bisulfite. The black oil that separates is extracted with ether and the extract is washed with water and saturated brine and dried over magnesium sulfate. The ether is evaporated and the residue is purified by distillation to obtain 2-iodo-4-(1-methylethyl)phenol (26 g.), b.p. 137°-140° C. (15 mm.).

Workup

  1. temperatureThe dark mixture is refluxed for 6 hours
  2. temperaturecooled
  3. extractionThe black oil that separates is extracted with ether
  4. washthe extract is washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe ether is evaporated
  7. distillationthe residue is purified by distillation

Sources & evidence

ORD record
ord-ae7a8e7c4e1a4279aefcef9bb37fde84
Source dataset
uspto-grants-1977_06
Patent number
US04029816

Reaction notes

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